Biomimetic Synthesis of the Pentacyclic Alkaloid (±)-Nirurine and Possible Biogenetic Rearrangement of a Precursor into (±)-Norsecurinine

Journal of the American Chemical Society

Volumn 114, Issue 1, 1992, Pages 382-383

  Magnus, Philip ^a,b   Rodriguez López, Julián ^a,b   Mulholland, Keith ^a,b   Matthews, Ian ^a,b  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84887319269     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00027a070     Document Type: Article

References (12)

1. Petchnaree, P.; Bunyapraphatsara, N.; Cordell, G. A.; Cowe, H. J.; Cox, P. J.; Howie, R. A.; Patt, S. L. J. Chem. Soc., Perkin Trans. 1 1986, 1551.
2. Snieckus, V. The Securinega Alkaloids. In The Alkaloids; Manske, R. H., Ed.; Academic Press: New York, 1973; Vol. 14, Chapter 11.
3. Heathcock, C. H.; von Geldern, T. W. Heterocycles 1987, 25, 75.
4. Jacobi, P. A.; Blum, C. A.; DeSimone, R. W.; Udodong, U. E. S. Tetrahedron Lett. 1989, 30, 7173.
5. Jacobi, P. A.; Blum, C. A.; DeSimone, R. W.; Udodong, U. E. S. J. Am. Chem. Soc. 1991, 113, 5384.
6. Himbert, G.; Fink, D. Tetrahedron Lett. 1985, 26, 4363.
7. Trifonov, L. S.; Orahovats, A. S. Helv. Chim. Acta. 1987, 70, 262.
8. Yoshida, M.; Hidaka, Y.; Nawata, Y.; Rudzinski, J. M.; Osawa, E.; Kanematsu, K. J. Am. Chem. Soc. 1988, 110, 1232.
9. Yamaguchi, R.; Moriyasu, M.; Kawanisi, M. J. Org. Chem. 1988, 53, 3507.
10. Comins, D. L.; Abdullah, A. H. J. Org. Chem. 1982, 47, 4315.
11. Van Rheenan, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 1973.
12. Barton, D. H. R.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1989, 30, 2619.